3,3-dimethyl-1-phenethyl-1-propyl-9,9a-dihydro-1H-oxazolo[3,4-a]indole-7-carboxylic acid

Base Information

Chemical Name:3,3-dimethyl-1-phenethyl-1-propyl-9,9a-dihydro-1H-oxazolo[3,4-a]indole-7-carboxylic acid
CAS No.:849480-37-1
Molecular Formula:C₂₄H₂₉NO₃
Molecular Weight:379.499
Hs Code.:

3,3-dimethyl-1-phenethyl-1-propyl-9,9a-dihydro-1<i>H</i>-oxazolo[3,4-<i>a</i>]indole-7-carboxylic acid

Synonyms:3,3-dimethyl-1-phenethyl-1-propyl-9,9a-dihydro-1H-oxazolo[3,4-a]indole-7-carboxylic acid

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Chemical Property of 3,3-dimethyl-1-phenethyl-1-propyl-9,9a-dihydro-1H-oxazolo[3,4-a]indole-7-carboxylic acid

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Technology Process of 3,3-dimethyl-1-phenethyl-1-propyl-9,9a-dihydro-1H-oxazolo[3,4-a]indole-7-carboxylic acid

There total 9 articles about 3,3-dimethyl-1-phenethyl-1-propyl-9,9a-dihydro-1H-oxazolo[3,4-a]indole-7-carboxylic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 87.0%

: 849479-86-3
(1R,9aS)-7-bromo-3,3-dimethyl-1-(2-phenyl)ethyl-1-propyl-9,9a-dihydro-1H-[1,3]oxazolo[3,4-a]indole

: 124-38-9,18923-20-1
carbon dioxide

: 849480-37-1
3,3-dimethyl-1-phenethyl-1-propyl-9,9a-dihydro-1H-oxazolo[3,4-a]indole-7-carboxylic acid

Guidance literature:: (1R,9aS)-7-bromo-3,3-dimethyl-1-(2-phenyl)ethyl-1-propyl-9,9a-dihydro-1H-[1,3]oxazolo[3,4-a]indole; With tert.-butyl lithium; In diethyl ether; pentane; at -78 ℃; for 0.25h;

carbon dioxide; In diethyl ether; pentane; at -78 - 0 ℃;
DOI:10.1016/j.tet.2004.12.041

Reference yield:

: 849479-97-6
tert-butyl (2S)-5-bromo-2-[(1R)-1-hydroxy-1-phenylethynyl-1-butyl]indoline-1-carboxylate

: 849480-37-1
3,3-dimethyl-1-phenethyl-1-propyl-9,9a-dihydro-1H-oxazolo[3,4-a]indole-7-carboxylic acid

Guidance literature:: Multi-step reaction with 4 steps

1.1: H₂ / Pd/C / ethyl acetate / 24 h / 20 °C

2.1: 11 mg / TFA / CH₂Cl₂ / 3 h / 20 °C

3.1: 72 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 4 h / 20 °C

4.1: t-BuLi / diethyl ether; pentane / 0.25 h / -78 °C

4.2: 87 percent / diethyl ether; pentane / -78 - 0 °C

With hydrogen; tert.-butyl lithium; pyridinium p-toluenesulfonate; trifluoroacetic acid; palladium on activated charcoal; In diethyl ether; dichloromethane; ethyl acetate; pentane;
DOI:10.1016/j.tet.2004.12.041

Reference yield:

: 79815-20-6,78348-24-0
(S)-indoline-2-carboxylic acid

: 849480-37-1
3,3-dimethyl-1-phenethyl-1-propyl-9,9a-dihydro-1H-oxazolo[3,4-a]indole-7-carboxylic acid

Guidance literature:: Multi-step reaction with 10 steps

1.1: sulfuric acid / 6 h / 80 °C

2.1: 31.4 g / CH₂Cl₂ / 20 °C

3.1: 93 percent / NBS / dimethylformamide / 2 h / 0 °C

4.1: 83 percent / i-propylmagnesium chloride / tetrahydrofuran / 0.5 h / -10 °C

5.1: 25 percent / tetrahydrofuran; diethyl ether / 1.5 h / 0 °C

6.1: 85 percent / tetrahydrofuran; diethyl ether / 0.25 h / -78 °C

7.1: H₂ / Pd/C / ethyl acetate / 24 h / 20 °C

8.1: 11 mg / TFA / CH₂Cl₂ / 3 h / 20 °C

9.1: 72 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 4 h / 20 °C

10.1: t-BuLi / diethyl ether; pentane / 0.25 h / -78 °C

10.2: 87 percent / diethyl ether; pentane / -78 - 0 °C

With N-Bromosuccinimide; sulfuric acid; hydrogen; tert.-butyl lithium; isopropylmagnesium chloride; pyridinium p-toluenesulfonate; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; pentane; 5.1: Grignard addition;
DOI:10.1016/j.tet.2004.12.041